Here are my numbers for ORD and MDW. May update at some point.
What will be a somewhat coolish start on Monday will give way to a hot day with a ton of sun, though dews look to remain comfortable. I'll go 95 at ORD and 98 at MDW for Monday.
Tuesday is the big day. A warm start (warmer than modeled) will create a nice launching pad for temps with plenty of sun once again. For me, this day is almost a no-brainer that MDW will exceed 100. The big question is what happens at ORD? I went back and forth on this one. Based on apparent tendencies lately, it lowers confidence in just how hot it will get there. That being said, I'm predicting the first *official* 100 degree day in Chicago since July 2012. My calls: 100 at ORD and 103 at MDW. Would note that I would not be shocked to see MDW even go just over this lofty number, but each degree above 100 is a rarer and rarer thing so I didn't want to get too carried away.
Tldr version:
Mon: 95 ORD, 98 MDW
Tue: 100 ORD, 103 MDW